Formaldehyde → Diethyl phosphonomethanol

HRID 2372092Notes

Reaction equation

HRID 2372092 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[CH2:9]=[O:10]>C(N(CC)CC)C>[OH:10][CH2:9][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 3780918Diethylphosphite

Product 1

HCID 76513Diethyl phosphonomethanolYield 60%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

To a 2 liter, round bottomed flask fitted with a nitrogen inlet were added 500 grams (3.6 mole) of diethyl phosphite (Aldrich), 120 grams (3.8 mole) of paraformaldehyde (Baker) and approximately 6 milliliters of triethylamine. The mixture was stirred overnight at room temperature but no visible reaction had occurred so approximately 10 milliliters more of triethylamine was added and the mixture was slowly warmed to 90° C. The solution was heated for approximately an additional hour, filtered hot and distilled. 320 grams of a liquid product corresponding to a 60% yield was obtained.

Workup

  1. customTo a 2 liter, round bottomed flask fitted with a nitrogen inlet
  2. customno visible reaction
  3. additionwas added
  4. temperaturethe mixture was slowly warmed to 90° C
  5. temperatureThe solution was heated for approximately an additional hour
  6. filtrationfiltered hot
  7. distillationdistilled

Sources & evidence

ORD record
ord-5847b38ceb8549c3a8f4c287a26fe910
Source dataset
uspto-grants-1992_03
Patent number
US05097057

Reaction notes

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